2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-12,12a-dihydro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (500 mg, 1.22 mmol) in toluene (7 mL) was added DDQ (552 mg, 2.43 mmol). The mixture was stirred at 80° C. for 2 hours. Then it was concentrated in vacuo, the resulting residue was purified using prep-HPLC to provide 6-(2-(benzyloxy)ethyl)-2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (44 mg, yield: 9%). 1H-NMR (CDCl3, 400 MHz) δ 7.32˜7.43 (m, 5H), 7.22˜7.28 (m, 1H), 7.11˜7.20 (m, 3H), 6.80˜6.86 (m, 1H), 6.65 (t, J=6.4 Hz, 1H), 4.48 (dd, J=8.0 Hz, 1H), 4.51 (d, J=12.0 Hz, 1H), 4.46 (d, J=12.0 Hz, 1H), 3.55˜3.62 (m, 1H), 3.25˜3.33 (m, 1H), 2.15˜2.23 (m, 1H), 2.02˜2.12 (m, 1H). MS (M+H)+: 409.

Provenance & Evidence